Potassium Carbonate → HCID 178483976, compound

HRID 1507632Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:7]=[C:8]([SH:18])[NH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:5])C.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:27][CH2:28][N:29]([CH3:31])[CH3:30].[OH-].[Na+]>CCO>[CH3:30][N:29]([CH3:31])[CH2:28][CH2:27][S:18][C:8]1[NH:9][C:10]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)=[C:6]([C:4]([OH:3])=[O:5])[N:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

5-(4-Fluoro-phenyl)-2-mercapto-1H-imidazole-4-carboxylic acid ethyl ester (3 g, 11.28 mmol) was dissolved in EtOH (30 mL) at RT. K2CO3 (6.23 g, 45 mmol) and (2-chloro-ethyl)-dimethyl-amine HCl salt (1.54 g, 10.72 mmol) were added. The mixture was stirred at 50° C. for 48 h. It was then concentrated and the residue was dissolved in THF/water (20 mL each) at RT. NaOH (2 g, 50 mmol) was added. The mixture was stirred at RT for 12 h. It was then concentrated to remove most THF and the pH of the solution was adjusted to ˜5 using 3 N HCl. The mixture was concentrated and residue was purified by prep HPLC. Lyophilization of pure fractions afforded 1.1 g pure 2-(2-dimethylamino-ethylthio)-5-(4-fluorophenyl)-1H-imidazole-4-carboxylic acid. LC-MS [M+H] 310.2.

Workup

concentrationIt was then concentrated
dissolutionthe residue was dissolved in THF/water (20 mL each) at RT
stirringThe mixture was stirred at RT for 12 h
concentrationIt was then concentrated
customto remove most THF
concentrationThe mixture was concentrated
customresidue was purified by prep HPLC

Sources & evidence

ORD record: ord-5c46c3474c174076b364ee015fa78e83
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221805B2

Reaction notes

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